I just set up a bunch of IFTTT recipes to trigger when random stocks go up/down by 1% in a day, and then get it to push-notification me a question like "what are you doing right now?"

I should only get one every couple of days they way I configured it (I think,) so perhaps requires more stocks. I wrote a different question onto each one, so I could easily get different reminders on the same day.

If anyone else knows a better randomness generator for IFTTT (I couldn't seem to use "someone followed me on twitter" as a trigger...) then pipe up!

I have a Python script that runs on my home computer. It runs on a 1 minute chron job and randomly sends a text message (via Verizon's phonenumber@vzwtext.com address) to my phone to check what I'm working on. The difficulty is that this system (on Verizon's end) seems a bit unreliable. I've been thinking about putting together an iOS app to send random push notifications to check what I'm working on. Would there be interest from others in this?

I also have it set up so when I reply to the text message it logs it into a spreadsheet. My plan was to do some machine learning on my productivity. Haven't gotten around to that part yet though.

IFTTT can send texts, and also works with the Pushover[1] app (not free) which collates push notifications like this. You can also send it notifications yourself programmatically - check out their API to see if you can link it up to your python script.

You might want to check out iDoneThis[2], which send you an email at the end of the day asking what you did. (I used it for about a month and then gave up, and it's less random, but it does log your responses.)